


i just want you (to take me where your heart is)

by strayycatss



Category: Anne of Green Gables - L. M. Montgomery, Anne with an E (TV)
Genre: Alternate Universe - College/University, Alternate Universe - Modern Setting, F/M, First Time, Fluff and Smut, Nervousness, Porn with Feelings
Language: English
Status: Completed
Published: 2021-03-01
Updated: 2021-03-01
Packaged: 2021-03-13 00:29:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 9,050
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29767956
Author URL: https://archiveofourown.org/users/strayycatss/pseuds/strayycatss
Summary: "Anne’s never done this before, but she really, really wants to do it with him."ORAn attempt at a realistic first time, and all the thoughts and feelings that accompany it.
Relationships: Gilbert Blythe & Anne Shirley, Gilbert Blythe/Anne Shirley
Comments: 14
Kudos: 135





	i just want you (to take me where your heart is)

**Author's Note:**

> PLEASE READ: Hello! This is a 'first time' fic, but it is also an examination of Anne's own thoughts and feelings about sex in general. Since I attempted to keep it somewhat realistic, there are mentions of self-doubt, awkwardness, and an anxiety attack. Please keep this in mind. Don't worry – this is a happy story, so it is also full of lots of love, and lots of patience. 
> 
> Title comes from 'Take Me Where Your Heart Is' by Q, which is practically all I listened to while writing this.

There’s a lot of things Anne’s never done before.

She’s never been skydiving, never tried pineapple on pizza, never been to Europe. She’s never broken a bone, never failed a spelling test, never put a good book down unless she absolutely had to. 

While some things are out of her control, a lot of what she hasn’t done is by choice. She likes having agency that way. 

When it comes to the fact that she’s never had sex, it’s for the same reason. 

Even if, at 21-years-old, she honestly thought she would have by now. It seems that everyone else at Redmond has. Sometimes, sex itself feels like an inescapable topic, whether it be through serious discussion in her gender studies seminar, or overhearing lewd conversations in the dining hall, or even in wine-fueled evenings with her oldest friends. She can’t tell if it’s actually everywhere, or if her own lack of experience makes her acutely aware of it.

Once upon a time, her friends would hardly speak of it in more than whispers, and even shunned her for a week in middle school when Anne had dared to broach the subject. Then in high school they were all curious, using sleepovers to study issues of Cosmo that Jane had swiped from Prissy, and once triple dog dared Anne to ask Gilbert Blythe about the “steps” (she didn’t, but was so mortified that she ended up shunning _him_ for a week without any explanation). By the time they graduated, a few of the girls had already been intimate with a partner, a few were looking forward to gaining experience in college, and a few were content to wait as long as it took. 

Now, it seems like Anne’s the last of her friends to take that next step. Even Ruby - sweet, innocent Ruby who still giggles at sex scenes in movies - had shyly confided to Anne that she and Moody had “done it”, and thankfully hadn’t offered any other details that Anne didn’t want to know (after all, it was _Moody_ ). All of her friends had confided in her when it happened for them, and she feels warmth and gratitude to be so trusted. She also feels relieved to know that, for the most part, they’d all had relatively positive experiences. 

The downside was that after their own admissions, her friends would stare at her expectantly, waiting to hear of experiences that she couldn’t share because they didn’t exist. She knows, truly _knows_ that it’s nothing to be embarrassed about, yet her cheeks would burn every time she had to admit to still being a virgin. 

Virgin. What a loaded word.

It’s one she’s mulled over often enough. The more she thought about it, the more it lost its meaning. After all, wasn’t virginity just a societal construct designed to place worth on young women? And when factoring in the different kinds of partners one could have, wouldn’t the textbook definition become murky? Most of all, was it really even _that big of a deal?_ Anne prides herself in her pursuit of being a woman of the world, and knows she has plenty of better things to do than dwell on the metaphysical significance of losing your v-card. 

Funnily enough, it’s Josie who offers her the most reassurance about the whole ordeal. After a particularly long discussion on her couch one night, where Anne self-deprecatingly admitted to being bothered by the concept and her own lack of experience, Josie had asked, “Aren’t you the person who said ‘Women are not made whole by men. Women are made whole the moment they enter this world’?” 

It was significant for Josie to ask that, and they both knew it. For Josie to say those words back to her, her point had been made. “Yeah, I did.”

Josie just shrugged. “Then get over it and buy a vibrator.”

And so she did. With dark sunglasses and her red hair tucked up into a hat, Anne had gone to a shop far away from campus and took a step towards learning about herself. It had been a fun, albeit awkward exploration, and through getting to know herself, she figures that it shouldn’t matter if her experiences aren’t the same as others so long as she’s still having fun. 

Yet, when her classmates seem so blasé about the subject, when the girls she grew up with (the same ones who once couldn’t even discuss holding hands without dissolving into a fit of giggles) tell her all about their nights, Anne still can’t help but feel like she’s been left behind.

If she’s honest with herself, it’s not for lack of opportunity. If she’s extra honest with herself, it’s because it never felt _right_.

There had been Charlie at a party freshman year. Nice, boring Charlie, who, while she didn’t view as a romantic prospect, would probably make for an okay first time just to get it out of the way. When they made out in the bathroom, he’d fondled her breasts over her blouse, and that felt kind of nice, and he ran a hand over her jeans to squeeze her rear, and that felt nice too. Then he’d grabbed her hand and cupped it against the bulge in his pants, and Anne became so mortified that she immediately left the party to hole up in her dorm room for the rest of the weekend.

Thankfully, she didn’t run into Charlie again for weeks, and when she did he greeted her as if nothing had happened. In hindsight, he had been taking shots all night and probably toed the line on blacking out, which made Anne all the more glad nothing major happened. She respected herself enough to know she deserved more than a drunken bathroom hookup, and respected Charlie enough to know it wouldn’t have counted as consent if he’d been that inebriated. After that, she decided that moving forward she’d treat the experience with a little more care. 

Then, there was Roy. Charming, polite Roy who had been her boyfriend for part of sophomore year, and was the person with whom she honestly expected to experience all of her firsts. He was the first boy to see her in just her underwear, the first boy to take off her bra, the first boy to explore the most sensitive part of her with his fingers (the first time they tried this, he’d briefly cringed at the feel of hair between her legs. Anne began shaving every day after that). He was also the first boy to ever tell her he loved her, and while Anne thought that would be enough to help her take that next step towards physical intimacy, it still couldn’t break down the steel fortress of her mental barriers. 

It was late one night when they were fumbling in the dark of his room, going farther than Anne’s nerves ever allowed them to before, that she really thought it might finally happen. They had made it as far as Roy settling over her, his weight barely pressing her body against the sheets, when Anne felt the inevitable anxiety attack hit. Roy had been understanding about it, giving her space and respectfully averting his gaze when she put her clothes back on, but Anne knew he took it as a rejection. They’d laid there awkwardly once she eventually calmed down, neither saying a word as the distance on the mattress grew between them.

“I guess I just don’t understand,” He admitted the next morning. “We’ve taken it slow, and I don’t think I’m being too pushy. I even told you I loved you.”

“Is that why you said it?”

“No, I just… don’t know why it didn’t help.” 

Anne didn’t know either, and the relationship ended when his front door closed behind her. She had made it back to the apartment she shared with Diana before breaking down into tears, allowing her bosom friend to gather her in her arms and stroke her hair until her cries dissolved into exhausted hiccups.

“I practically led him on and I still couldn’t follow through,” Anne sniffled. “What is _wrong_ with me?”

“You didn’t lead anyone on. Sharing yourself like that is a privilege, and it’s one that you don’t owe him or anyone else,” Diana said firmly. Then, in a softer tone, she’d said, “And nothing’s wrong with you. You’ll know when you’re ready. You’ll know.” 

Now, there’s Gilbert. Kind, patient, infuriating Gilbert who knows her better than most people, yet for some reason still openly considers her one of his favorite people in the world. The same Gilbert who, despite the cold shoulder she gave him for years, despite the arguments she still likes to pick, despite all their misunderstandings... still likes her. Still blushes when people tease them, still glances at her with a look that she might recognize as hope if he wasn’t so quick to look away.

He’s the same as he’s always been, but he’s different. 

Months after she and Roy had broken up, she and Gilbert had been treating themselves to a late dinner after a particularly rough week of exams. They’d been doing a lot of things together lately, just the two of them, and as they sat across each other in a booth of their choice since they were the only customers at that hour, Anne had briefly entertained the idea that they were the only two people in the world. Gilbert didn’t bat an eye when she dipped her fries in his milkshake, and she only grumbled a tiny amount when he snatched their bill and whipped out his card, holding them up high where she couldn’t reach until their waitress came back. 

He’d walked her home after; he always does when they’re done hanging out, regardless of the hour. Anne had been in the middle of roasting him relentlessly for spilling ketchup on his shirt, and when he was done laughing, he stopped them in the middle of the sidewalk. They’d looked at each other for a moment, and he’d said her name quietly in a way that made it sound like a question. Anne hadn’t stopped him when he slowly, _carefully_ raised his hand to her cheek, and she hadn’t stopped him when he leaned in to kiss her so lightly that she wasn’t sure it happened at all. 

“I– I just wanted to try that once,” He admitted, pulling away and looking nervous. “Just so I could stop wondering what it’d be like.”

Anne had raised her fingertips to her mouth, tracing them lightly as her heart hammered wildly. He’d taken a step back to give her space, and she’d stepped forward to close it again.

That was a month ago. They’ve kissed every day since.

Kissing Gilbert is unlike anything she’d imagined. Not that she’d imagined kissing him before – the thought may have crossed her mind a few times, but she’d passed it off as moments of lunacy. She had certainly imagined kissing in general, and her romantic nature would make her get lost in fantasies about all the ways one could kiss and be kissed. Although she enjoys kissing and had enjoyed the majority of the kisses she’d shared with others, none of them quite lined up with what her imagination and favorite poetry told her to expect. 

Kissing Gilbert doesn’t line up with them either, but that’s okay. His kisses are better. She’d once earnestly asked why girls had to wait for boys to kiss them first; if she wanted to kiss a boy, couldn’t she just kiss him? With Gilbert, she does. She kisses him when he meets her before class with two coffees in hand, pulls him close after spirited debates, finds his lips with hers over their books as they study on his living room floor. It’s just natural. It’s actually so natural, that it boggles her mind how it can simultaneously ignite something in her that’s so hot, she’s sure he’ll burn when he touches her.

Which, being touched by Gilbert is also unlike anything she’d imagined. Charlie had touched her, and Roy had touched her, and she’s definitely touched herself, but Gilbert’s touch is somehow different, somehow _more._ When previously she would stop another’s hand in its pursuit of mapping out her skin, she finds herself wanting Gilbert to keep going. With each brush of his knuckles down her shoulder, each press of his fingers to her waist, she feels another mental barrier crumble, and it only adds to the multitude of possibilities she sees within Gilbert Blythe. 

That’s not to say she doesn’t still have her insecurities; the body positivity she championed for others never quite extended to herself. For years growing up, she’d been told she was homely, that nobody would ever love a freckled, red-haired orphan who talked too much, and she’d believed them. Gilbert had met her when she was a preteen, all gangly limbs and crooked teeth, so she finds it hard to believe him when he insists he’d harbored a crush on her even then. Sometimes, it’s hard to believe him when he insists he finds her even more beautiful now. Although she’s grown and thankfully finished puberty, she still feels as though she’s stuck in a perpetual awkward phase, and admitted as much to him one afternoon when she felt too unattractive to even pull her hoodie down. 

To her surprise, Gilbert had confessed that he doesn’t like his dark circles, or how unruly his hair is, or how he’s the shortest guy in their group of friends. The fact that he would be self-conscious about his appearance had surprised her; he seemed so untouchable by such petty insecurities that she’d forgotten he's only human too.

“But I like those things about you,” She argued.

He’d held his hands out and raised his eyebrows expectantly, as if waiting for her to solve the last step of a complicated equation. She had smacked him on the arm before kissing him again, as if that’s how she was always meant to wipe the smirk off his face. 

Considering it’s only been a month since Anne acknowledged her feelings for him, it seems almost inappropriate to desire him as much as she already does. She wants to attribute the expedited timeline to their familiarity, since what they have is borne of a friendship she’d already held so dear, full of comfort and respect that had been earned and nurtured. Still, she finds it rather ridiculous that she’s suddenly paying extra attention to the lean muscle in his forearms, or how the feel of his hand on her lower back when he holds a door open for her does more to turn her on than it probably should.

To desire someone this way feels new, but _feeling_ so desired is even newer. Sure, she knows she’s been desired before, but it always seemed to come with a catch. With others, they’d liked her in spite of something. With Gilbert, he likes her in spite of nothing. 

She kept waiting for him to find something repulsive about her, and was certain it would happen when they were making out in her bedroom and she felt his fingers gingerly trail up her inner thigh. Instantly, she remembered the look on Roy’s face the first time he touched her there, and she clamped her hand around Gilbert’s wrist to prevent him from going any higher.

“Wait!” She’d panted, and Gilbert removed both hands from her immediately. 

“Sorry, sorry, I should have asked, sorry,” He panicked, scooting away from her in a way that was almost comical.

Anne felt her face go red as she mumbled, “No it’s fine, it’s just… um, I haven’t shaved.”

Gilbert blinked down at her, then sighed in relief. “Oh, is that all?”

“What do you mean _is that all_?”

“It doesn’t bother me, if that’s what you’re worried about,” He’d explained with a shrug. Then, his hand flew up to rub at the back of his neck as he rambled, “Sorry, that’s assuming it has anything to do with me at all. It could easily be a personal preference, and I get that, but um, for what it’s worth, I haven’t shaved either so–”

Anne had cut him off with another kiss, and grabbed his hand to put it back under her skirt. 

Since then, they’ve become more confident in not only touching each other, but in communicating what they like. Anne learns that he likes extra attention to be paid to a particular spot on his neck even though he’s kind of ticklish, and that he likes it when she straddles him so their hips are pressed together _just so_. Gilbert learns that she likes it when he stops to kiss her sternum before moving lower, and that when he curls his fingers a certain way, she’ll moan his name. They’ve always been so curious and inquisitive, so it makes perfect sense to Anne that they would be the same about each other’s bodies. 

Despite their explorations, it still takes a while for her to work up the nerve to tell him she’s a virgin. She thought back to Josie, and how acknowledging such a fact is nothing to be ashamed of, but she was still anxious about admitting it to Gilbert. She knew he wouldn’t judge her, but she also knew that he himself wasn’t a virgin. He’s older than her and has been in more relationships, and she’s afraid she’ll disappoint him. 

“Does that bother you?” She’d asked a few days ago, leaning against the counter as he tried (and failed) to not burn their dinner. 

“Of course not,” He’d said so sincerely that it made her bite her lip. “Why would it?”

“I don’t know. I mean, I’m sure you’ve done it plenty of times. You’re probably an expert compared to me.”

At that, Gilbert had put the spatula down and looked up at the ceiling, eyebrows drawn in the way that told Anne he was trying not to show just how worried he really was. “I… don’t really think it’s a good thing to compare. And honestly, Anne, I’ve really only had sex a handful of times. So I don’t want… if it happens, whenever that is, I don’t want you to go into it with these expectations that I’ll be good at it right away. Because honestly, I probably won’t know what I’m doing at first, and you still kind of make me nervous.” 

Anne had pulled the pan off the burner for him before it blackened any further, stirring around the vegetables as she thought over his words. Then, she set it aside so she could pull his face down to hers and kiss him with a reassurance that they apparently both needed. He kissed her back sweetly, looping an arm around her waist in a way that felt like an anchor.

“You still kind of make me nervous too,” She had murmured against his lips. “But in a good way.”

He kissed her again before grabbing the panhandle to resume cooking. Anne hugged him from behind and said, “And for the record, I’m still gonna have expectations.”

“That doesn’t surprise me,” He’d laughed quietly. “And what are they, Miss Shirley?”

“My expectations will be that we both enjoy it because we both want it, and that you’ll make sure I’m okay every step of the way,” She had declared with conviction because she knows it's true. Then, she’d pressed her cheek to his shoulder and said, “From you, I’ve come to expect nothing less.”

Gilbert had only responded by squeezing the hand that she’d rested over his heart. 

After that conversation, Anne felt something shift. It’s like an energetic hum that envelopes them now, growing louder and more insistent with every form of contact until Anne’s unable to hear anything else. 

He’d promised to come over to study today, and the knock on her door had made her jump. Now, the sight of him standing there in her entryway, looking so at home as he shrugs out of his red plaid jacket and hangs it on the hook next to hers, makes the hum reappear in earnest. When he looks up from untying his boots and shoots her a smile that makes her toes curl, the hum becomes deafening. 

Anne suddenly understands why she hadn’t been ready to be intimate with anyone sooner. Before, she’d thought that just getting it over with would be enough. Then, she’d thought that simply being wanted by someone would be enough. Maybe even loved, if she was lucky. But even with those factors in place, she still hadn’t known what was holding her back.

What she realizes as Gilbert stands before her, looking so happy to see her, is that it’s different this time because not only does he love her, but she loves _him_ , too. She trusts him implicitly. Even if they weren’t dating now, even if things went wrong, even if they don’t last (although something deep within her suspects they could), she trusts Gilbert enough to cross that threshold with him. The realization is so exciting that it’s almost overwhelming. 

Under her gaze, his cheeks turn an inviting shade of pink to match the wind-chapped tip of his nose, and her mind’s made up. 

Anne’s never done this before, but she really, really wants to do it with him. 

She’s in the middle of trying to figure out how to tell him as much when he steps forward to greet her with a kiss. It’s a sweet peck that ends too quickly, but when she pulls him back in by the collar and opens her lips against his, he responds eagerly until they’re sighing and swaying. 

“Hi,” He breathes between kisses, brushing her hair back from her face. “I brought over my notes, but if you’d rather do this right now–”

“I’d rather do this,” Anne confirms, tugging on his collar again for emphasis.

Gilbert cradles her face with cold hands, and even though they help to soothe her burning cheeks, she desperately wants to warm him up. Her hands reach around and brush down the soft fabric of his sweater, pausing briefly at the hem before dipping underneath to rub warm palms along his lower back. He shivers under her touch, and she’s certain that she’s chasing the chill away.

“That feels nice,” He murmurs, burying his face in her neck to plant hot kisses there. Anne lets her eyes fall shut at the feeling of it, enjoying the way his hands run down her sides, grazing her ribcage and smoothing over her waist. When he tugs her closer so that their hips are flush together, Anne realizes she’s too impatient to keep making out in her entryway.

“Gilbert?”

“Hmm?” He hums in acknowledgment, nuzzling his nose along her jaw. 

She doesn’t say anything for a moment; even if her mind wasn’t foggy from his attentions, she still wouldn’t be sure how to say what she’s thinking without feeling totally awkward about it. Anne’s never considered herself particularly coquettish, and feels like her sex appeal is precarious at best. Although they’ve gotten better at communicating, she sometimes fears she’ll kill the mood when she talks too much, or when she’s too explicit instead of playing coy. Because of this, she wishes she could communicate that she’s ready through the way she kisses him, or that something in her touch would let him know what she wants. 

When she takes too long to respond, Gilbert pulls away to peer down at her. He already looks deliciously disheveled with his pink cheeks and rumpled sweater, and she likes the way his chest rises and falls with every breath. But his eyes, heavy-lidded and pupils blown, are so full of romance that she remembers she doesn’t need to be self-conscious. It’s _Gilbert_ after all, and he’s always been so eager to hear exactly what’s on her mind.

“Did you forget what you wanted to say?” He teases, raising one eyebrow expectantly.

She wants to hit him with another slate for that, but since she doesn’t currently have one on standby, she simply blurts out, “I want to have sex with you.” 

She may as well have hit him with a slate. His face looks the same as it did when she hit him all those years ago: shocked, red, just a little bit excited. His gawking could almost be funny if she wasn’t dying for him to say something.

“Today,” She clarifies. “Like right now.”

His grips tightens on her hips at that, and his tongue darts out to wet his bottom lip. It’s a positive reaction so far, but the way his eyes dance across her face makes him look far too confused for something she’d just been so clear about. One of his hands reaches up to gently trace her cheekbone with his thumb, and he asks, “Are you sure?”

Anne leans into his touch and squeezes his wrist so she can hold it in place. With her other hand, she lets herself be a bit bolder by trailing her fingers along his waistband until they’re playfully fiddling with his belt buckle. “I’m ready if you are.”

They study each other for a moment, and Gilbert swallows hard. Then, he swoops in to kiss her again, and the enthusiasm makes Anne gasp. She abandons his belt to throw her arms around his neck, and he winds both arms around her so tight that she has to stand on her toes. When they finally break apart after a moment, he rests his forehead against hers and says, “Yeah. Yeah, I am.” 

Anne’s certain that her grin is just as dopey as his. They giggle together for a moment, eager and disbelieving and completely wrapped up in each other, and Anne’s so relieved that she’s doing this with her best friend.

The giggling doesn’t last long; when her fingernails scratch lightly at the curls at his nape, his eyes darken again, and Anne gives him another lingering kiss. She pulls back, enjoying the way he chases her lips, and says, “So if we’re currently of the same mind–”

“We definitely are–”

“And you know where my bedroom is–”

“I definitely do–”

Anne laughs again when he mouths at her neck. “Then can we get out of my hallway? No one else is home, but I don’t think either of us wants Diana to walk in on anything.”

Gilbert laughs too, all excitement and nerves, and makes her squeak in surprise when he lifts her easily. Her legs automatically latch around his waist, and a giggle escapes her throat when he kicks his backpack out of the way to walk them to her room. It’s oddly thrilling to be held by him like this, and she’s reminded of all the stories she’s read about heroines being swept off their feet. She wonders if any of them felt as secure as she does in the safety of Gilbert’s grip. 

He pauses every few feet to kiss her again, which makes the moment they finally stumble through her bedroom door fill Anne with so much anticipation that she refuses to let go of him until he deposits her on the bed. The moment she falls back on the mattress, clutching him close as he hovers over her, Anne vaguely realizes that this is it. She intends to do exactly what she’d obsessed over for so long now, and she intends to do it with him.

She’s nervous, but she’s not scared. 

The beginning is familiar; she and Gilbert have wandered to each other’s bedrooms enough times now for her to know what comes next. Like the way he kisses down her neck, open-mouthed and slow despite how quick his fingers work to unravel her braid. She knows he likes her hair, knows he likes to get tangled in it, knows pulling it loose might always be his first step in undressing her. Anne likes this little ritual they’ve created. 

She also knows he’ll typically wait for her to make the first move when it comes to taking off clothes. He’s patient that way, or maybe he’s just scared he’ll push her too fast. Frankly, the feel of his lips trailing along the collar of her blouse is way too _slow,_ and Anne pushes him away for a second so she can impatiently peel off her shirt and throw it across the room. She grabs for his sweater and undershirt next, and they both giggle again when his head briefly gets stuck in the neck hole. 

“Just rip my head off, why don’t you,” Gilbert scolds with a cluck of his tongue.

“Okay,” Anne shrugs, and buries her hands in his curls to _tug_.

The groan that erupts from his chest shoots straight between her legs, and she quickly pulls his face back to hers, completely uninterested in allowing any space between them. She wants to tug his hair to hear him groan again, but she’s learned that even though he sometimes likes it a bit rough, he likes it in small doses. Instead, she lets her foot trail up the back of his thigh until ler leg is hitched around his waist again, and pulls his hips down against hers in a way that makes him reflexively thrust against her.

The feeling of how hard he already is makes her pause. She’s felt him hard before, has even seen him, touched him with her hands, but right now she wants to get used to the idea of what it might feel like to have him _inside_. Gilbert pauses too, letting her adjust to the feeling of being pressed under him like this, and she’s thankful for his intuition. Anne experimentally rolls her hips up against his, and soon they rock together, creating a tantalizing friction that has her impatience growing again until Gilbert pulls back abruptly. 

“Wait, sorry, I–,” He apologizes, looking absolutely stricken. “I actually don’t have a condom, I should’ve– if I had known I would’ve– I can run to the store real quick–”

“No, no, it’s okay,” Anne assures him. “I have what we need.” 

He all but collapses back on top of her. “Oh, thank God.” 

“Thank the student health clinic,” Anne snorts. “I grabbed a bunch the last time I went.” 

He quirks an eyebrow. “A bunch, huh?”

“You know, just in case,” Anne tries to say nonchalantly. “But... let’s just see how this time goes?”

Gilbert’s face softens at that, and the way he smiles down at her with hooded eyes is so tender that it makes her chest ache. He leans down to kiss her again, so sweet as he whispers, “Sounds good to me.” 

With the logistics out of the way, it doesn’t take long for mouths and hands to wander once more. Gilbert takes his time kissing down her chest, pushing aside her bra straps and mouthing at the pink indentations they left in her soft skin. Anne arches her back to quickly undo the bra, knowing he still struggles with the hooks, but lets him take it off the rest of the way and drop it to the floor. Then, after taking a moment to smooth his hands up her torso and against the sensitive underside of her breasts, Gilbert wets his lips again before closing them around one peaked nipple. 

Anne finds it almost absurd how just that small amount of suction can send her reeling. She lets out a quiet moan, grabbing for his hair so she can keep him exactly where he is. His hand reaches up to play with her other nipple, tweaking it between two fingers and squeezing her gently in a way that’s almost too gentle, but that’s okay – she can appreciate that despite her insistence and curiosity, he’s still too timid to be rougher with her yet. His mouth, however, feels perfect; the way his tongue lazily swirls around her, soft lips tugging against her until he releases her rosebud peak with a wet pop, has her squirming beneath him. 

“I like that you have freckles here, too,” Gilbert admits, voice low as he kisses the valley of her breasts. “I like that when you blush, it spreads all the way down to here.” 

Anne doesn’t like either of those things, but she likes that _he_ likes them, so she won’t argue about it. In a rare moment of submission, she doesn’t want to argue with him at all. She just wants to see what he’ll do next. 

Still, she’s riled up enough that she can’t help but goad, “Oh yeah? What else do you like?” 

The grin he shoots her can only be described as wicked. “I’m glad you asked.” 

She used to think Gilbert was too smug and insufferable for his own good. Then over time, she learned that he was kind and generous, perhaps sometimes to a fault. As she watches him crawl his way down her body, kissing every inch of skin that fascinates him, Anne realizes that she gets to be on the receiving end of the very best parts of those qualities. 

“I like how you bite your lip when you look at me sometimes,” He says, unbuttoning her jeans to slowly tug them off. Anne kicks out of them to help him, giggling when her foot almost collides with his head. He grabs her ankle and deadpans, “I also like that you’re still actively trying to give me concussions.”

Anne just rolls her eyes at that, but her mouth falls open when he kisses her calf, hot breath moving up her leg as his hands brush closer and closer to her panties with each pass. “I like that you wear floral underwear because that’s just so _you_ , and I like the sound you make when I–”

His fingers trace over her crotch, taking a second to locate her clit over the fabric, and Anne lets out a soft cry when he does. Gilbert ducks to hide his grin against her hip, as if he doesn’t want to make her mad at how she’s just proved him right. 

He keeps rubbing circles while the other hand caresses her thigh, having learned pretty quickly that it’s too overwhelming if he goes straight for her folds without letting her ease into it first. Anne can feel herself getting wetter, knows _he_ can feel her getting wetter even through the cotton of her panties, and as he strokes her just like she taught him, her breathing starts to become ragged. 

“A little to the left,” She huffs. “No, my left, a little higher – _oh._ ”

He squeezes her thigh when she bucks against his hand. “I like it that you’re a little bossy in general, but especially when we’re like this. I _really_ like it.”

Anne’s smart retort turns into a gasp when he applies more pressure and kisses her over the fabric, and she lifts her hips up to drag her underwear down. She doesn’t think twice about it, but a moment later, in the fading light of her room as the sun starts to set outside, she realizes she’s completely naked in front of Gilbert for the first time ever – completely naked in front of _anyone_ for the first time ever. Despite her certainty in him, her self-consciousness comes flooding back in an instant, and she has to resist the urge to curl in on herself to cover up. 

The look on her face must give her away, because Gilbert, whose hand had been hovering over her center as if he was about to proceed, suddenly pulls away to rest on the mattress beside her. He reaches up to tuck her hair behind her ear, and the previous headiness of his gaze is replaced by concern. 

“Are you okay?” He checks in, voice quiet and comforting. “Do you wanna stop?”

Anne takes a measured breath, and grabs his hand to squeeze it. “No, it’s just… I’m _naked_.”

She feels stupid when the words leave her mouth. He’s seen her down there before under bunched-up skirts and panties pushed aside, so she doesn’t know how to explain what she’s feeling about it now. After a moment though, he seems to catch on to her meaning. 

Gilbert stands up off the bed, making sure she’s watching as he slowly, deliberately starts to take off the rest of his clothes. He lets out a short, nervous laugh when his hands fumble with his belt buckle, and Anne loves him all the more for it. When he finally sheds his boxers, he sits beside her again. 

“There, now I’m naked too,” He says, laying back but keeping just a bit of space between them. “Is that okay?”

“Yeah,” Anne breathes, looking up and down his body. From their previous trysts, she’s seen him in bits and pieces, but never all of him. Now, as her eyes roam over him uninhibited, from the blush in his cheeks, to the skin on his chest, to the dusting of dark hair beneath his navel, all the way to the leaking tip of his cock, she decides she quite likes seeing him all at once. She meets his eyes again, and sees the nervousness she feels reflected back at her. Even though it’s not his first time being seen naked, it’s his first time being seen naked by _her._ This is new territory for him, too. 

The thought grounds her again. 

“Can I touch you?” She asks, tentatively reaching for him. He nods eagerly, and when she wraps her fingers around his length in a gentle grip, he lets out a sigh that reignites the spark inside her. She starts stroking up and down, and doing this for him eases them back into the familiar; she’s done this for him a few times now, and grows more confident each time she does it. 

“I like it when I do this and you get this little quirk in your eyebrows, like you can’t believe it’s happening,” She says, surprising them both by how low her voice comes out.

“Because I _can’t_ believe it’s happening,” He laughs, making her laugh too. She twists her wrist just so, and his hips jerk. “Fuck.” 

Anne starts to move her hand faster and peppers kisses across his collarbone, enjoying the way his chest rumbles when he groans. His hand cards through her hair to cradle her neck, and when she swipes a thumb teasingly over his tip, he pulls her face up to his to crash their lips together. Anne abandons his cock to wrap her arms around him so he can roll them onto their sides, and their kiss turns all tongue and teeth. 

They rock together for a moment until Gilbert’s hand drops between them, gently rubbing her clit again before dipping lower. His fingers stroke up and down between her folds, and when she gives him her own vigorous nod, he pushes his index finger inside. When he starts slowly thrusting, Anne moans louder than she has yet, and Gilbert presses his forehead to hers.

“You’re so fucking beautiful,” He murmurs, enjoying the way her breath hitches when he curls his finger on an outward stroke. He lets her get used to it, then carefully adds another finger. “I like that you trust me enough to share this part of yourself with me.” 

Anne presses down onto his hand, her own hands scrambling for purchase against his shoulders as the tension starts to coil in the pit of her stomach. His wrist keeps knocking between them, so she hooks a leg over his to give his hand more room to move, and the adjustment is _glorious_. Gilbert’s fingers pump in and out of her steadily, and he doesn’t mind when she drops her fingers to her clit to help him out. Her eyes search for his as she gasps, “I like how safe you make me feel.”

At that, he kisses her again desperately, and before she knows it, she’s coming. She honestly hadn’t expected to; it’s happened only a few times so far with him, and she thought the pressure of this moment would get in the way. Instead, she releases a surprised cry as Gilbert holds her through it, letting her ride his fingers as the pleasure pulses through her body. When she comes down, legs trembling slightly, she sighs in contentment and lets her head loll against his shoulder. 

Gilbert beams down at her, face lit up so damn bright as he spreads his fingers against her stomach. “Was that…?”

“Yeah,” She breathes. 

He bites the inside of his cheek, looking quite pleased about it in a way that still annoys her _just_ a little bit, so she retaliates by lazily running a finger up the length of his shaft. Even in her haze, she’d noticed him discreetly palming at it, and she can’t have that, not when he’s just made her feel so good. He shudders under her featherlight touch, ticklish as he is, and pulls Anne closer so she’s half-splayed on top of him. With her leg still hooked over his, the tip of his cock nudges her inner thigh, and the air between them is suddenly so charged that her mouth goes dry. 

They gauge each other’s reaction, and it hits Anne that this is happening _now_. It’s happening right now, right here in the safety of her own bed, right here in the safety of Gilbert’s arms, and she wouldn’t have it any other way. 

She drops her head to kiss him again, summoning all of her confidence as she asks, “Should we grab a condom?” 

Gilbert’s eyes scan over her face, searching for any traces of hesitance, any lingering uncertainty. He looks so serious all of a sudden, and Anne hears how much he cares for her in the way he says, “Only if you’re still sure.”

She nods. “I’m sure.”

It settles over them, and Gilbert lifts his mouth to hers to kiss her soundly in a way that feels like a promise. He then releases her so she can fish through her bedside drawer for a condom, but keeps a light hand on her leg as if he’s reluctant to let her go. The fingers on his other hand thrum in a stuttering beat against the bedsheets, and in a rush of nerves, they speak over each other in soft voices: 

“Are you sure you don’t need more foreplay? I can go down on you, or– we can use your vibrator, or–”

“It’s okay, I already– you already made me–”

“I know, I just wanna make sure you’re ready–”

The ‘ _so it doesn’t hurt’_ goes unspoken, but Anne hears it anyways in the thinly-veiled anxiety of his tone. She already knows it might hurt, but hearing how worried he is about it strangely helps to calm her own fluttering nerves.

“I think we’ll be okay,” She assures him, crawling back to brush the curls off his forehead. “If it hurts or I need to stop, I’ll tell you. If you need to stop, you’ll tell me.”

“Okay,” He exhales, grabbing her hand to press a quick kiss to her knuckles. “Okay.”

It becomes a flurry of sound and movement after that, a cacophony of crinkling foil and rustling sheets and hushed “ _I love you’s_ ” as they get into position. Anne figures that one day, the minutiae of preparing for what they’re about to do will become second nature, but right now, she’s keenly aware of every small detail: how the cap popping off her bottle of lube sounds too loud in the quiet of the room, how the mattress springs shift and creak underneath them as they get comfortable, how Gilbert’s fingers hold the just tiniest tremor as he helps her settle on top of him.

For all that her friends had said about their first times, for all the things written in the articles and books and discussion boards that she’s read, nobody had ever mentioned that it would feel this precious. 

For that, she kisses him again. 

It takes her a second to find the right angle on top of him, both of them huffing out soft giggles as she adjusts her knees and sets her hands on his stomach. When the tip of him catches against her, Anne’s breath catches in her throat, and she automatically looks to Gilbert for safety.

She should’ve known he’d already be looking to her. 

“I like how wide and bright your eyes get when we’re about to try something new, how you look at me to make sure I’m right there with you,” He murmurs, reaching up to run a finger down her hairline and cup her cheek. “And I am, Anne. I am.”

Slowly, Anne lowers her hips, and takes the tip of him easily. After that, even with how slick she already is, the stretch of him starts to sting. It makes her thankful that she’s on top for this, because she can sink down inch by inch at her own pace with gravity to help her out. Meanwhile, Gilbert lays so still underneath her that she’s sure he’s holding his breath too, and when she reaches the hilt, they both let out a shaky exhale. 

“You okay?” He whispers, hands moving in soothing strokes from her thighs to her lower back. 

“Yeah, I just need a sec,” She whispers back, breathing in time with each stroke of his hands. The sting is manageable, but the sensation of feeling so full in this way is entirely foreign. She tries lifting herself a bit, and even though her nose scrunches slightly, there’s a small improvement when she settles back down. She continues to move slowly on top of him, and with each tentative rise and fall, the discomfort eventually ebbs away. 

Beneath her, Gilbert hasn’t once taken his eyes off her face. Even when a slightly firmer roll of her hips has him inhaling sharply and letting his head fall back against the pillows, he still refuses to look away. The fact that he’s _inside of her_ right now almost doesn’t seem real, but even Anne’s vivid imagination couldn’t conjure the way he gazes up at her, slack-jawed and absolutely moon-eyed as he grips the sheets in an effort to stay still. 

It makes goosebumps erupt across her skin, and suddenly, desperately, she needs whatever he can give her _._

“I think I’m okay now,” Anne breathes out, grabbing his hands to place them back on her waist. “It’s okay, you can move.” 

Gilbert takes a deep breath, then flexes his fingers along her skin as he starts carefully thrusting upwards. It takes them a few fumbling attempts to establish a rhythm, but soon they’re moving against each other in a way that has light, airy gasps escaping from Anne’s lips. She leans down slightly to brace her hands against his chest, and her hair falls in a red curtain around their dazed faces.

He gently squeezes her hip. “Hi.”

She smiles shyly back. “Hi.”

Gilbert cranes his neck up to kiss her, snaking an arm around her waist as he goes so he can keep her steady when he slightly picks up the pace. Anne cries out at the adjustment, trying her best to match him thrust for thrust. By now, the sting and discomfort has all but disappeared, and the hard, heavy drag of him at this angle feels fucking fantastic.

“Still okay?” He rasps, hips slowing a bit after the way she cried out. 

“Gil, _yes_ ,” She pants, grinding down on him impatiently. He resumes their pace, and she tilts her head back with a sigh. He runs a hand up from her thigh to her chest, kneading across her breasts and trailing over her collarbone before tugging her hair over her shoulder. It reminds her of a time he’d tugged on her braids so many years ago, and her throat constricts with emotion at how far they’ve come. 

“Look at you, look how beautiful you are. Most beautiful person I’ve ever met,” He babbles, gazing up at her with such heavy lids that his hazel eyes are the darkest she’s ever seen them. “God, Anne, you feel– fuck, I still can’t believe this is happening.” 

Maybe it’s just a knee-jerk reaction to being reminded of the first time he’d tugged on her hair, or maybe she needs confirmation that this is really happening too, but Anne can’t resist reaching for his wrist to pinch him. He hisses in pain before laughing, and the sounds send a shot of heat down her spine.

“It’s really happening,” She says dreamily, although the sentence morphs into a groan when the tip of his cock brushes her g-spot. Gilbert continues to whisper sweet nothings to her every few thrusts until the only words he can form are her name and “ _fuck_ ”. Their breathy moans and the sound of skin on skin fill her quiet bedroom, and Anne wonders if these four walls will hold the echo of this moment when it’s over. 

Which, it might be over soon. Her rhythm starts to falter, not exactly from an approaching orgasm (as incredible as it feels, she’s not sure she’ll be able to come again), but from the apparent effort that is required for being on top. Gilbert, meanwhile, is so flushed and taut beneath her that she’s not sure how much longer he’ll last either. She’s surprised that it makes her heart sink – she’s waited so long for this experience, and she’s not sure she’s ready for it to end just yet.

“Slow down,” She gasps.

He stops moving altogether, eyes widening in concern. “What’s wrong?” 

“Nothing,” She shakes her head. “I just– I want to remember every single thing about this.”

Gilbert’s eyes soften with complete understanding, and she once again wonders how she could’ve ever doubted that he was a kindred spirit. Anne takes her time soaking it all in; the warmth of his skin, the placement of their hands, the sight of where they’re connected between her legs. He’s still hard as a rock inside her and covered in a light sheen of sweat, but he waits so patiently for her, just like he always has, and Anne knows that he’s committing this to memory too. 

“I love you,” She says, voice high and thick and leaving no room for argument. 

She feels it in the hammering heartbeat under her fingertips, sees it in the smile that illuminates his face. His voice comes out softer, but just as thick. “I love you, too.” 

Anne leans down to kiss him, holding him tight so he can roll them back on their sides. He starts thrusting again, hovering over her slightly, forehead pressed to hers, and Anne realizes it’s okay that this first time will come to an end. There will be more times with him, many more times where they’ll only get better, and Anne wants them all. Now that they’ve done it this once, the possibilities are endless, and it _thrills_ her. 

“Faster,” She commands, drawing her knee up a bit so she’s more open.

Gilbert immediately obliges, pumping into her harder and faster than he has yet, and the motion has her releasing tiny whines with every other thrust. It stokes something inside of her, a fire that has her clutching at him and insisting, “Touch me.”

His hips snap harder at the tone of her voice, his hand automatically running down her backside to squeeze at her ass. Anne giggles at the look on his face, and says, “You said you like it when I’m kind of bossy.”

“I do,” He confirms with a breathless chuckle, snaking his hand down between her legs to rub just above where he thrusts in and out of her. “But I think it’s safe to assume that I like everything about you.” 

They continue to move together like that, hands and lips and hips working as a team to bring them closer to the edge. Anne feels his puffs of hot breath against her neck, feels him struggling to keep the pace, and she likes that recognizing when he’s close is yet another thing she’s learned about him. 

“ _Anne_ ,” He pants, and it sounds like a plea as his hips stutter.

“I’m here,” She gasps, cradling his face in her hands. “It’s okay.”

He attempts a few more deep thrusts, then empties himself into the condom with a groan. Anne holds him through it, just like he had for her, and when his weight somewhat sags against her, she’s overcome with emotion. Her thoughts ricochet through her brain like a pinball: She, Anne Shirley-Cuthbert, just had _sex!_ With _Gilbert_ _Blythe_ _!_ And it was good, and he was kind, and she loves him, she loves him, she _loves_ him.

They stay in that position for a moment to catch their breath, Gilbert too tired to move and Anne unwilling to let him go. Eventually, he presses a lingering kiss to her lips, then quicker ones to her cheek and hairline before propping himself up on one elbow. 

“You okay?” He asks quietly, fingertips running up and down her arm. 

“Yeah,” Anne sighs, placing a hand over his so she can squeeze it. “You?”

He smiles and ducks his head to kiss her again. “Yeah.”

There’s a lot of things Anne’s never done before. She had never laughed with someone while hunting for discarded clothing, never shared the cramped space of her shower, never bickered over what kind of takeout would be best for a post-coital meal. She had never been pulled in for kisses while getting dressed, never been thanked so sweetly, never been held so carefully when the lingering wobble in her legs makes it difficult to walk. 

Now, she has. 

She’d expected to feel different after having sex for the first time. What she didn’t expect was to feel more like herself. As she cuddles up to Gilbert later while they eat, legs draped across him and talking with their mouths full in an intimacy that’s been earned, she knows this is exactly how it was always meant to happen. 

Anne had never done this before, but she’s really, really glad she did it with him.

**Author's Note:**

> *Ladybird voice* WHO THE FUCK IS ON TOP THEIR FIRST TIME??
> 
> So. I was not ready for how difficult it is to write smut. A million and a half kudos to the people in this fandom who write and share it. My hat is off to you!
> 
> Thank you so much for reading if you've made it this far! I know this story covers a more sensitive subject matter, but I tried to make it as believable as I could. That means a healthy dose of awkwardness to go with the tenderness, so I hope it came off well.
> 
> Some elements of this were partially inspired by personal experience (like feeling weird about not having done certain things by a certain age). I just want to remind anyone who's feeling like Anne in the beginning that everybody experiences things differently, and will experience them in their own time (or can decide to not experience them at all). Take your time, check in with yourself, and don't compare yourself to others. You're you, your experiences are yours, and you're wonderful. 
> 
> Thanks again for reading!


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